


lose your honor

by fairysylveon



Category: Borderlands (Video Games)
Genre: Intercrural Sex, Lingerie, Loss of Virginity, M/M
Language: English
Status: Completed
Published: 2020-10-27
Updated: 2020-10-27
Packaged: 2021-03-09 04:15:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,608
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27218500
Author URL: https://archiveofourown.org/users/fairysylveon/pseuds/fairysylveon
Summary: Jack is quiet for several moments, and Tim can feel his face getting hotter and hotter as Jack stares at him intently. “...Huh.Really didn't think you could get any sexier, but you're avirgin?Holy shit, Timmy. That’s hot as hell.”The way Jack is looking at him like he’s a piece of meat has Tim's heart hammering in his chest. Is Jack actually interested in him now? Does Jackfinallywant to fuck him?God,he hopes so. But just in case he’s wrong, Tim tries to hide his excitement by rolling his eyes and acting blasé towards Jack’s flirting. “Ofcourseyou have a thing for virgins.”“Doesn't everybody?”Tim crosses his arms and gives Jack a pointed look. “Only the creeps.” Which is probably true, but unfortunately for Tim, that’sreallyturning him on.---pwptim's a virgin, jack's gonna fix that
Relationships: Handsome Jack/Timothy Lawrence
Comments: 3
Kudos: 44





	lose your honor

**Author's Note:**

> here's "outdated views on the concept of virginity: the fic"  
> 

Tim has gotten used to Jack’s casual flirting. Jack has been hitting on him since the day they met, and while it  _ used _ to make him wildly uncomfortable, he actually _ likes _ it now. Jack is charming and handsome; it hadn’t taken long for him to win Tim over, and Tim can't deny the way he gets flustered when Jack compliments him, or the way his entire face turns red at Jack's more lascivious comments.

He can, however, deny how many times he's frantically jerked off thinking about his boss. Jack's suggestive comments never actually  _ leading _ to anything has left Tim so sexually frustrated that he  _ frequently _ excuses himself to the bathroom, and stays there for a suspiciously long time. And what’s worse is how little it takes to rile him up; sometimes  _ all _ it takes is Jack rubbing his shoulder and telling him he did a good job. 

Which means he's probably in  _ serious _ trouble right now, because Jack is touching him and  _ he’s way too close. _ Jack’s hand is warm and heavy on Tim’s shoulder, keeping him still as he holds Tim by the jaw and slowly examines every angle of his face.

“Wh-what are you doing?” Tim is desperately trying not to focus on the fact that Jack's hands are on him, because he knows if he does, he’ll almost _ certainly _ get hard; he’s spent too many nights imagining those big hands all over him _ not _ to.

Jack doesn’t seem to notice his discomfort, or he just doesn’t care. “What's it look like, kiddo? Makin’ sure everything's still accurate. Can't have you running around with imperfections.” Tim had told him once that he used to have freckles, and he wonders briefly if Jack is checking for those.

“Oh, r-right.” Tim knew that, or he _ should _ have, but he still can't help the disappointment he feels. The shame of letting himself get carried away in his fantasies makes him flush, and he wishes more than anything that Jack wasn't looking at him so closely.

Jack takes a half step back and raises an eyebrow, but he doesn’t let go. “What the hell are blushing like that for?” he asks, a teasing smile pulling at the corner of his mouth. Fuck, does Jack know?  _ Fuck. _

“Oh, uh-- you're just-- you’re just so close, it's a little embarrassing being stared at like that,” Tim says, giving Jack a half truth. He does  _ not _ want to deal with the humiliation of Jack finding out that he's actively trying to fight off a boner; he’d  _ never _ live it down.

Jack huffs a laugh, and Tim can’t tell if it’s just because he likes teasing him, or if he knows that Tim is hiding the truth.  _ Fuck, fuck, fuck. _ “You blush like that when you're bangin’ hot chicks? You better not be making me look bad, Timtam.” 

Where the hell did _ that _ come from? As flirty as Jack can be, he’d never actually brought up Tim’s sex life before. Fuck, he  _ definitely knows, _ doesn’t he? “I-- I'm not,” Tim insists, and god, he  _ really _ wishes Jack would let go of him.

“Oh yeah? And how’re you managing that, pumpkin?”

Tim's face feels so hot he thinks he might burst into flames. He doesn’t want to be talking to Jack about his sex life in the first place, but it’s even  _ more _ embarassing to admit that he’s never had sex. “I-- I haven't, uh, picked anybody up yet. So I haven't really had a chance to--”

“Wait wait wait, nobody? Not a single person? You've looked like _ this,” _ Jack gestures at him for emphasis, “for months now, and you haven't fucked  _ anybody? _ You gotta be pullin’ my leg, c'mon.” Jack lets go of him and tilts his head inquisitively, grinning like he knows Tim is messing with him. “I’m not actually mad about the blushing thing, so seriously, you’re kidding, right?”

Tim lets out a quiet sigh of relief, and he hopes Jack doesn't notice. If Jack somehow  _ hasn’t _ figured it out, Tim does  _ not _ want to explain why he didn’t want Jack touching him. “N-no, I'm-- I'm serious, I haven't fucked anybody.”

“Wait so-- you're tellin’ me, your face from before-- you got more pussy looking like  _ that _ than you do now? That doesn't make sense pumpkin, have you  _ seen  _ us?”

Tim blushes again and looks away, too embarrassed to meet Jack's eyes. He’s not going to spell it out for Jack any more bluntly than _ I haven’t fucked anybody. _ “That’s not what I said.”

Jack is quiet for several moments, and Tim can feel his face getting hotter and hotter as Jack stares at him intently. “ _...Huh _ . Really didn't think you could get any sexier, but you're a  _ virgin? _ Holy shit, Timmy. That’s hot as hell.”

The way Jack is looking at him like he’s a piece of meat has Tim's heart hammering in his chest. Is Jack actually interested in him now? Does Jack  _ finally _ want to fuck him?  _ God, _ he hopes so. But just in case he’s wrong, Tim tries to hide his excitement by rolling his eyes and acting blasé towards Jack’s flirting. “Of  _ course _ you have a thing for virgins.”

“Doesn't everybody?”

Tim crosses his arms and gives Jack a pointed look. “Only the creeps.” Which is probably true, but unfortunately for Tim, that’s  _ really _ turning him on.

Jack laughs softly, then steps back into Tim's space and settles his hands on Tim’s hips as he presses their chests together. “Creeps, huh?” 

Tim’s brain short circuits and can't seem to form words, and when Jack's hands slide up Tim's sides, Tim makes a surprised sound that's  _ embarrassingly _ close to a whimper.

Jack leans in to brush his lips over Tim's ear, and oh  _ god,  _ he's so  _ close. _ Despite Jack's obvious interest, Tim is determined not to get a boner, because Jack could very easily be messing with him, and he doesn’t think he could handle that humiliation. “So how about it? Want daddy to pop your cherry, Timmy?”

_ Holy shit. _ Okay, so much for not getting a boner. 

Tim's face turns bright red. He can feel his dick quickly stirring with interest, and he’s sporting a half chub before he can even  _ think _ about trying to control his arousal. “Oh god--” 

Jack lets out a low, rumbling laugh, and Tim shivers at the sound. Jack's fingers push under Tim's sweater, groping at his chest with a pleased hum. Tim bites his lip, arching into the touch as Jack dips his head to kiss along Tim's jaw. “I need an answer, baby.”

Tim's breath hitches, and he tilts his head to give Jack more room. He’s  _ way  _ too turned on to pretend he isn’t desperate, so he nods frantically. “Y-yes, yesyesyes, god, please Jack.”

Jack tries to pull away, but Tim grabs onto his shirt and insistently pulls him back in. He _ just _ got Jack to start touching him, he doesn’t want it to stop so soon, and he’s  _ far _ too caught up in the moment to realize Jack might be pulling away for a reason.

Jack laughs at his eagerness and gives him a reassuring pat on the shoulder. “Relax, pumpkin. C’ere, got lube in my desk,” he says as he turns and heads up the stairs.

Of  _ course _ he does. Feeling a little dazed, he follows Jack to the desk and leans against it as Jack rummages through a drawer.

Jack pulls out a small bottle of lube and sets it on the desk, then gestures for Tim to come closer. Tim obediently moves to stand beside Jack, and before Tim can even process what’s happening, Jack has spun him around and bent him over the desk.

It takes Tim’s brain a second to catch up, but when it does, he looks over his shoulder at Jack and raises an eyebrow. “You're taking my virginity... at your desk?” He knows Jack is an impatient man, but he thought they'd at  _ least _ make it to Jack's reading nook or something. Then again, he supposes he’s been acting pretty impatient too, so maybe Jack assumed Tim wanted to be fucked over the nearest flat surface. Tim would have definitely picked somewhere more comfortable if given the choice, but as long as Jack  _ finally _ fucks him, he won’t complain  _ too _ much.

“What, you want rose petals scattered around or something?” Jack asks, as he runs a hand between Tim’s shoulder blades.

“Actually… that’d be really nice, yeah,” Tim says, because it would be, if Jack was considerate enough to do something like that for him.

Jack shrugs, his hand trailing down Tim's back. “Maybe next time.”

Probably not, because Jack's almost certainly not a romantic, and next time won't even have the benefit of being special. Tim doesn't really know how he’d wanted his first time to go, but he still feels a little disappointed. But it doesn’t matter all that much; he'll get over it, because he's been fantasizing about Jack for  _ months, _ and he's  _ finally  _ about to get what he wants.

Jack unceremoniously shoves Tim’s pants and underwear to his knees, making Tim shiver as the cool air hits his ass. He whistles at the sight, loud and obnoxious, before running a finger over the cleft of Tim's ass.  _ “Look _ at you, princess, holy shit.”

Tim blushes and hides his face against the sleeve of his sweater. Jack had changed almost everything about Tim's body to match his own, but he'd mercifully left Tim's ass and genitals alone. His praise is genuinely for _ Tim, _ not himself, and the realization has Tim pushing his ass higher into the air, hopeful that Jack will compliment him again.

Jack laughs softly and gives Tim's ass a little slap, then spreads his cheeks to get a better look at his hole. Tim squirms under the scrutiny, but it's a nice feeling; Jack looking at him so closely and clearly liking what he sees is flattering to say the least.

Jack reaches for the bottle of lube, and Tim's stomach flutters with nerves and excitement. It's _ happening!  _ after all that fantasizing, after all those nights nearly jerking himself raw to the thought of Jack fucking him, it's  _ finally _ happening!

Tim hears the cap pop open, and he braces himself for the feeling of slick fingers against his hole. He's never fingered himself before, so he's a little nervous, but he's sure Jack will make it good, and he wants it more than _ anything. _

Then, he feels thick, slick fingers sliding between his thighs. 

Wait… what?

“What are you doing?” Tim asks curiously, looking down to watch Jack’s hand slide between his legs.

“Change of plans, sweetheart.” Jack finishes smearing lube between Tim's thighs and wraps a hand around his own dick, giving himself a few languid strokes as he appreciates the view.

“Change of plans? But-- but you're still gonna fuck me, right? Please say yes--” Tim blurts, then flushes bright red at his own forwardness and hides his face against his sleeve again. He’s embarrassed by his desperation, but he just can’t help it.

Jack laughs and gives the back of Tim’s thigh an appreciative squeeze. “Don’t worry, there’s _ no way _ I’d pass up taking your V card, princess.”

Tim lets out a relieved sigh. Thank  _ god. _

“But not today.”

Oh  _ goddammit. _

Tim looks back at Jack with wide eyes. He’s wanted this for  _ so long, _ he doesn’t  _ want _ to wait longer. “No, Jack-- nonono _ no, _ you _ said--” _

Jack shushes him and runs a soothing hand up the length of Tim’s back. “Relaaax pumpkin, I'll still get you off. I just wanna save you for a better time, y'know? Maybe my birthday, I mean, what better way to celebrate than with a pretty virgin, am I right? Of  _ course _ I’m right!”

Tim  _ really _ doesn’t want to wait; he’s  _ already _ waited, and Jack’s birthday isn’t for  _ months. _ But right now he’s horny enough to agree to anything, if it’ll get Jack to touch him sooner. “I… Okay.  _ Okay, _ just--  _ please.” _

_ “There's _ a good boy,” Jack purrs. He grips Tim’s hips to keep him still, then shoves his dick between Tim's slick thighs with a low groan. Jack’s cock nudges up against Tim’s balls, making Tim whine and push down more firmly against his dick, desperate for more friction. Jack leans over him and presses his chest against Tim, then peppers kisses up the back of Tim’s neck as he roughly thrusts between Tim’s thighs.

Tim groans at the contact, overwhelmed by having Jack on top of him, and squeezes his legs tighter around Jack's cock, giving him a tighter hole to fuck.

He's rewarded with a moan and hot, heavy breaths in his ear as Jack rests his chin on Tim's shoulder. " _ That's _ it, baby," Jack purrs, and Tim shivers at the sound of his voice. Jack nibbles at Tim’s earlobe and pushes his hand up under Tim's sweater, large fingers sliding up to rub appreciatively over Tim's chest. 

Tim arches into the touch, gasping when Jack brushes over his nipple. His heart is pounding in his chest, and he’s so hard it almost  _ hurts. _ He thrusts almost uselessly back against Jack, unable to get any friction against his neglected dick, and unable to rub his ass against Jack’s cock. “God,  _ Jack, _ I wish you’d fuck me, I need you so  _ bad,” _ he whines, desperately grinding his balls against Jack’s dick, but it’s not _ enough. _

“I know, princess, I know,” Jack says, voice soft and low as he runs his hand up and down Tim’s side. “God I’d  _ love _ to shove my cock in your tight little ass, baby. Bet you feel  _ so _ good. You have  _ no idea _ how much I wanna fuck you through this desk and make you scream, Timmy.”

“Then do it, Jack, _ do it _ , fuck, it’s not  _ enough.” _

Tim can feel Jack’s cock twitch with interest between his thighs, but Jack has unfortunately already made up his mind. “Oh baby, I plan to. Just not today. Can you be patient for me? Can you be a good boy, sweetheart?”

Reluctantly, Tim nods. He doesn’t want to wait, but he  _ does _ want to be good for Jack.

“There you go,  _ such _ a good boy for me, pumpkin.” As if rewarding him, Jack slowly runs his hand down the length of Tim’s body, then wraps his thick fingers around Tim’s cock. Tim gasps, his hips thrusting into Jack’s fist involuntarily, his dick desperate for attention. Jack peppers kisses along Tim’s neck as he jerks him off, and it only takes a few slow, teasing strokes before Tim is moaning loudly, his hips stuttering forward as he cums messily over Jack’s hand.

Jack pulls his hand away, and his movement stills. Tim can  _ feel _ that Jack is staring at him, and he’s not  _ saying anything, _ what must he think? Oh god,  _ oh god.  _ Tim is so embarrassed he’s sure he must be  _ bright _ red, because he feels like his face is on fire. “Oh god, Jack, I’m so sorry, I just--”

But Jack cuts him off with a raucous laugh.  _ "Wow. _ I  _ barely  _ touched you, holy shit. That might be a record!"

Tim covers his face with his hands and groans miserably. Jack must think he’s  _ pathetic.  _ “Oh  _ god. _ I didn’t mean to-- I mean, I-I usually last longer when I’m-- god, I’m so embarrassed, I--”

_ “Relax, _ pumpkin, jesus. That was fuckin’ precious,  _ and _ hot as hell.” Jack pulls his dick out from between Tim’s thighs, and before Tim can even question it, Jack is sliding his cock into the cleft of Tim’s ass. “God, you’re so fuckin’ hot baby, I can’t _ wait  _ to fuck you.” Jack rubs the head of his cock against Tim’s hole, making Tim whine and arch his back.

Tim can’t get hard again yet, but his dick certainly makes a valiant effort anyway. “Stop _ teasing,” _ Tim says, nearly pouting.

But of course, Jack doesn’t stop. Instead, he leans back to watch as he ruts against the crack of Tim’s ass. _“Shit,_ princess, your ass is _perfect._ Can’t fuckin’ wait to feel your perfect virgin hole around my cock.” Tim can feel Jack’s cock twitch at his own words, and Jack's movements become more erratic as he squeezes Tim’s ass. “God I can't fucking wait to ruin you, baby. I'm gonna pop that cherry so hard you'll _never_ settle for anyone else-- _fuck._ Fuck, baby, I'm gonna cum all over you, sweetheart."

Tim thinks it's a  _ shame  _ he's not hard again yet, because  _ holy shit.  _ He moans, and pushes his ass back against Jack's cock as he nods desperately. "Fuck, please, I want you to cum on me Jack,  _ please,"  _ he begs, so carried away he's become completely shameless.

Jack groans, his hips jerking forward as he shoots thick ropes of cum all over Tim's ass. He pulls back, jerking himself through the rest of his orgasm and letting cum splatter across the back of Tim's thighs.

When he's spent, Jack leans back over Tim, panting as he presses kisses along Tim’s shoulder. 

Tim lets out a shaky breath. "Holy shit." He's never had sex until now, so maybe his perspective is skewed, but he thinks that might be the hottest non-fuck he'll ever have.

Jack chuckles, soft and rumbling. "Not too pissed off that I didn't fuck you, then?"

Tim lets out an amused huff. "No, I'm still kinda pissed about that, but… wow."

Jack stands up and pulls away, then gives Tim a _ hard _ pop on the ass. Tim yelps and moans, then slaps a hand over his mouth, his cheeks flushing pink.  _ Shit. _ Well… he just discovered a new kink.

Jack laughs again, and rubs a hand soothingly over Tim's ass. _ "Wow, _ you're kind of a slut for a virgin, y'know?" he teases, and Tim has a feeling that’s  _ great _ news to Jack.

  
  


\------

  
  


Tim is in Jack's reading nook during his lunch break the next day, sitting cross-legged on the chair as he finishes off his sandwich. Jack has barely acknowledged him the whole time, too busy with whatever he's working on to chat much. 

Which is why it's even  _ more  _ surprising when Jack breaks the silence to ask, "You ever fingered yourself?"

Tim has to fight not to choke on his food, and he stares at Jack incredulously. Sure, Jack had fucked his thighs the day before, but Tim is still caught off guard by Jack's bluntness.  _ "What?"  _

"You heard me. Answer the question, Timtam." Jack is looking up from his screen now, staring at Tim expectantly.

"N-no, I haven't," he says, hoping it's the answer Jack is looking for.

Jack gives him a disbelieving look and leans back in his chair, crossing his arms over his chest. "Not even last night? You seemed  _ real _ desperate pumpkin, you didn't go home and shove some fingers up that sweet ass? Or even go out and buy a dildo to bounce on so you could pretend it was me?"

Tim flushes pink and looks away, embarrassed and more than a little turned on now, thanks to Jack's vulgarity. "N-no, I didn't! Jesus, Jack, can't you be a  _ little _ less obscene?"

"Bet you jerked off so much you started to chafe though, huh?" Jack asks, an amused smirk on his face. 

Tim blushes harder. He's absolutely  _ not  _ answering that, even if it's actually kind of true.

"Yeah, thought so." 

"Is there a  _ reason _ you brought this up, or did you just wanna fuck with me?" Tim asks, frowning at Jack. God, what an asshole; he probably just wants to see Tim get flustered, and it’s definitely working.

"I just wanna make sure you're nice and tight for me, sweetheart. So no fingering yourself until  _ after  _ I've had my way with you. Got it?"

Tim rolls his eyes. Of  _ course  _ Jack is telling him what to do with  _ his  _ body. Tim has to admit that being ordered not to finger himself is kinda hot though, so he doesn't protest. "Got it."

"Oh, and one more thing. I got you something. C'mere," Jack says, waving him over.

Tim can only imagine what kind of gift Jack had gotten for him. With his luck, it's probably a chastity device or something, which would  _ really  _ throw a wrench in his plans to furiously jerk off again tonight. He takes the last bite of his sandwich and gets up to walk over to Jack's desk.

When he approaches, Jack pulls out a flat box and puts it on top of the desk. "You're gonna wear this when you come over. Go on, open it up."

Tim tilts his head curiously, then pulls the lid off the box. Carefully laid out inside is a pair of black lacy panties and a matching garter belt, both adorned with little yellow bows, along with a pair of sheer thigh high stockings. They're admittedly pretty cute, but... Tim doesn't really think he can pull them off. He feels like every time he tries to be sexy, he just ends up looking stupid, and he's worried that wearing these will have the same effect. He'll just have to deal with it though, if that's what Jack wants. "Uh, o-okay. I can do that," he says, blushing a little and hoping he won't look completely ridiculous. "...Anything else?"

"Nope! That's it.  _ Really _ lookin' forward to my birthday, babe," Jack says with a wink, and even if he  _ does  _ end up looking dumb in the lingerie, Tim definitely shares the sentiment.

  
  


\------

  
  


Jack feels damn near giddy when his birthday rolls around. It had been almost  _ impossible  _ to keep his hands off Tim for the last several months, and Jack had  _ strongly _ considered going back on his decision and bending Tim over the nearest flat surface  _ several _ times. But he  _ really _ wanted to save deflowering Tim for a special occasion, and it had been  _ so hard,  _ but today, all his self restraint is finally gonna pay off.

Tim lets himself in when he arrives, just like Jack instructed. Jack looks up from his spot on the couch and grins, spreading his arms wide as he stands to greet him. "Heya, princess, how's it hanging?" 

"Uh… it's a  _ little _ cramped right now actually, thanks for asking," Tim jokes, looking down at himself and shifting uncomfortably. 

Jack gives him a lecherous smirk and crosses his arms over his chest. "Yeah? You got 'em on, baby?"

Tim blushes and pulls down on the waistband of his jeans, giving Jack a peek of the panties underneath. "Y-yeah. But I-- I'm worried I'll look stupid," he admits, averting his gaze as he nervously plays with the edge of the lace.

Jack raises his eyebrows. He's surprised Tim is still nervous about shit like that after months of looking like Jack; Tim is goddamn sexy, and he deserves to know it. "Well, let's see then, huh?"

"Oh, uh-- okay..." Tim hesitates for a moment, then starts pulling his clothes off, tossing them into a pile on Jack's floor. When Tim is fully undressed, he looks away anxiously, and it seems like he's trying to make himself as small as possible. It’s almost like he's trying to hide, and Jack has no idea why, because he looks  _ fucking amazing.  _ The black panties and stockings are a stark contrast against his skin, and the suspenders on the garter belt make his thighs look  _ gorgeous.  _ The little yellow bows are a nice touch, too; Jack pats himself on the back for picking out such a cute set.

Jack closes the gap between them and puts his hands on Tim's face, making him look Jack in the eye. "You got no reason to be worried, pumpkin. You look sexy as hell."

Tim blushes, but gives Jack a sweet, shy smile. "Thanks, Jack... Oh! And happy birthday."

God, he's so fucking cute, Jack can't wait to fuck him into the mattress. "Thanks, handsome. Now come here, I got a surprise for you." Jack puts his hand on Tim's lower back, and guides him toward the bedroom, eager to get a reaction out of him. When Jack opens the door, he gestures at the room with a grin. Inside, the lights are dimmed slightly, and he's strewn rose petals across the comforter. "Well? What do you think?"

Tim's eyes go wide for a moment, but then he looks over at Jack with such a warm, fond smile that Jack immediately thinks the extra effort was well worth it. "Thank you, Jack. This is  _ so _ much more romantic than being shoved onto your desk," Tim says, laughing softly and leaning in to give Jack a sweet kiss on the cheek. 

The warm and fuzzy feeling in his chest isn't something Jack is used to anymore, and it kind of makes him uncomfortable, so he tries to brush it off quickly. "Yeah, well. Don't get used to the  _ romantic  _ part, I'm still gonna fuck your brains out."

Tim laughs again, louder this time as he makes his way over to the bed, and Jack shamelessly watches his ass as he goes. Tim sits down on the edge of the bed and lets his legs fall open invitingly, despite the timid expression on his face. "You better, I've been waiting  _ months  _ for this," he says, a light blush spreading across his cheeks.

Jack smirks and follows after him. "So have I, and lemme tell ya princess, it was  _ not _ easy to keep my hands to myself." And he can’t _ possibly _ resist now, so he reaches down to cup Tim's soft dick through the sheer, lacy underwear. 

Tim spreads his legs further, bucking up against Jack's hand as his dick begins to stir. _"I'm_ not the one who wanted to wait, remember?"

"Waiting just makes it better. Builds excitement and all that."

"I dunno, it probably got over hyped by now, I'll probably be disappointed," Tim jokes, grinning up at him. 

Jack huffs a laugh as he rubs Tim through his panties, until Tim's dick is tenting the underwear, precum leaking onto the fabric. "I want you to remember that little joke when you're begging for my cock later, 'kay princess?"

Tim seems to have lost interest in teasing, because his answer is just a jerky nod and a shaky exhale as he pushes up against Jack insistently, wanting more friction. 

Jack pulls his hand away, and Tim looks like he's about to complain, but Jack cuts him off. "Hurry up and get your ass in the air for me, pumpkin," he orders as he starts quickly pulling off his own clothing.

"Yes sir," Tim answers, nice and obedient, exactly how Jack wants him.

Jack watches appreciatively as Tim gets into position, putting his head on the pillow and sticking his butt up, presenting himself in those cute little panties like his ass is a gift for Jack to unwrap. Jack can't fucking  _ wait  _ to get his dick in that perfect virgin hole. 

As soon as Jack is fully undressed, he grabs the bottle of lube off the nightstand and crawls onto the bed, settling himself right behind Tim. He hums appreciatively as he takes in the sight of Tim; that pretty blush on his face, his arched back, the way he’s shoving his ass up high in the air, eager to show off for Jack.

And Jack is happy to give him the opportunity. “Lemme see, pumpkin,” Jack purrs, running his hand over the small of Tim's back. Tim shivers with excitement and reaches behind himself, pulling the lace to the side and exposing his hole to Jack's heated gaze. Jack whistles at the sight; he’s been dreaming of that perfect ass since their last encounter, and he’s  _ thrilled  _ about actually getting to play with it this time. “Bet you're  _ tight, _ aren't ya babe?” Jack presses his fingers against Tim's asshole and rubs gently, eliciting a soft whine in response. “You want daddy to finger your pretty hole open, princess?”

Tim lets out a shaky breath and nods eagerly. He buries his face against the pillow and desperately shoves back against Jack’s finger.  _ “Please,” _ he says, voice muffled.

“Never met such a slutty virgin before.  _ Listen _ to you baby, such a good boy,” Jack praises as he lubes up his fingers. The embarrassed whine Tim gives in response goes straight to Jack's dick. It's going to take a  _ lot _ of self control to work Tim open; all Jack wants to do is fuck into that tight little hole _ now.  _ But if Jack's going to pop Tim's cherry, he's damn well going to do it  _ right.  _ So instead, he starts slowly pressing the tip of his finger into Tim, nice and gentle. Tim tenses up slightly at the feeling, and Jack gives him a moment to relax before pressing in further.

Tim squirms and lets out a pleasured sigh, then turns his head to look over his shoulder at Jack. “Feels nice,” he mumbles.

Jack responds with a pleased hum. “Just wait 'til I get my dick in you, pumpkin,” he says, and angles his finger to rub against Tim's prostate. Tim jolts and presses his face back against the pillow, muffling his cry of pleasure. “How’s  _ that  _ feel, baby?”

“Good, _ so _ good. Fuck, Jack, go  _ faster, _ I want your dick in me,  _ please,”  _ Tim babbles.

Jack laughs softly and nudges another finger against Tim's hole. Tim’s eagerness is hot as hell, but as much as Jack wants to, he can’t just skip prep altogether, especially not for Tim’s first time “No can do sweetheart, it’ll hurt if I go too fast.”

Tim lets out an impatient whine. “I don't care, just  _ hurry.” _

“You really _ are _ a slut, damn.” Jack starts pressing the second finger in slowly, using shallow thrusts to work him open. “I really lucked out with you, didn't I princess? Pretty little virgin, but  _ such _ a needy whore.” Tim just groans in response, so Jack keeps talking. “Promise I'll make it good. Just be a little patient, 'kay pumpkin? Can you do that for me, baby?”

“I’ve  _ been _ patient for months Jack,  _ please,” _ Tim begs, flushing at his own desperation as he rocks himself back onto Jack’s fingers.

And fuck, Jack can’t deny him any longer. He’s so gorgeous like this, with his ass in the air, holding his panties out of the way, a sweet blush on his face while he pleads for Jack’s cock. How can Jack resist?  _ “Fuck.  _ Fuck,  _ okay,  _ I can't say no to you, babe.” Jack pulls his fingers out and runs a hand over Tim's ass before giving it a slap, making Tim jerk forward and groan softly. "Flip over, princess. Daddy wants to see more of that pretty face."

Tim, obedient as ever, does as he's told. He turns over and spreads his legs, and Jack's eyes are drawn to the tent in Tim's panties. Tim's dick is drooling precum through the lace, and Jack can't resist running his finger over it. Tim gasps and bucks his up into the touch. "You're making a  _ mess, _ Tim. Such a pretty little whore, fuck,  _ look _ at you. You want it bad, huh baby? You want daddy's cock now?"

Tim's blushes bright red, but he nods frantically. "Yes, yesyesyes,  _ please, _ Jack!  _ Please _ fuck me already, I need it so bad."

And Jack needs it, too. He's almost rubbed himself raw thinking about that sweet ass over the last few months; he's just as eager as Tim is. He gives his neglected dick a few strokes as he reaches for the lube, then quickly slicks himself up. "I got you, princess. Gonna fuck you so good, Timmy." Jack grips the back of Tim's thighs and shoves his legs open. Tim dutifully grabs onto his thighs to hold them in place, and Jack reaches down to pull those cute panties to the side again, then nudges his dick up against Tim's hole as he focuses his gaze back on Tim's face.

Tim is flushed, his eyebrows drawn together and his lips parted as he stares down the length of his body to watch Jack line himself up. "Yesyesyes, put it in, please--"

Tim cuts himself off with a gasp, and Jack groans as he slowly slides his cock into Tim's hole. He's  _ so fucking tight, _ and knowing he's deflowering his pretty doppelganger makes this first push into him feel fucking  _ amazing. _

"Yesss, fucking  _ finally, _ oh god,  _ Jack--" _

As soon as he's balls deep in the tight heat of Tim's ass, Jack has to give himself a moment to calm down, because he's almost certain he'll shoot off too quickly if he doesn't. "Hooooly fuck, Timmy. You're so perfect, baby, so fucking  _ perfect, _ you feel so good, pumpkin." 

Tim hooks his legs around Jack's waist and pushes up against him with an impatient whine. Jack drags his cock almost all the way out, then starts rocking into Tim with slow, shallow thrusts. "Needy little slut, aren't you, princess?" 

Tim moans, nodding in agreement as he throws his arm over his eyes.

"Nuh-uh, none of that shit," Jack says, reaching to pull Tim's arm away from his face and pinning his wrist beside his head. Tim looks up at him with a sweet, pleading expression, and Jack thinks with a face like that, it'd be easy for Tim to wrap Jack around his finger, at least as long as Tim keeps spreading his legs. "What's that look for, baby?"

Tim bites his lip, looking embarrassed but adorably needy. "Want you to fuck me harder,  _ please _ Jack…"

And as much as Jack would  _ love  _ to keep making Tim beg for more while he's writhing on Jack's dick, the desire to fuck Tim through the mattress wins out. So Jack snaps his hips forward, driving his cock into Tim at a brutal pace, his hips slapping against Tim's ass with every thrust. Tim shouts, and when Jack doesn't relent, his mouth falls open on a loud moan.

"Fuck, fuck, fuck, Jaaa-ack!"

"That's it, baby. Scream my name princess, lemme hear you," Jack purrs as he slams into Tim with harsh, punishing thrusts.

Tim must be eager to please, because he groans and chants Jack's name over and over, then grabs Jack by the shoulders and pulls him down insistently. Jack lets Tim drag him closer, and Tim presses their lips together in a rough, hungry kiss. Jack moans and bites Tim's lip, and Tim wraps his arms around Jack to scratch down his back. 

Jack growls and breaks the kiss, then dips his head to lick and bite at Tim's neck, and Tim hisses when Jack’s teeth sink into his skin. Jack can't fucking  _ believe  _ this is the same shy Tim that gets flustered when Jack flirts with him. And he's  _ still _ got that gorgeous blush on his face, even as he gives Jack’s hair a harsh tug in retaliation. Tim's fervor is hot as hell, and Jack's  _ thrilled _ to be the first person to see this side of him.

_ "So _ fuckin' pretty, Timmy.  _ Look _ at how worked up you are, you've been  _ aching _ to have your cherry popped, haven't you, babe?"

Tim nods, jerky and frantic. "Yes,  _ yes, _ been waiting  _ so long, _ Jack.”

"Don't worry pumpkin, daddy's gonna take care of you," Jack promises as he slams into Tim relentlessly, every thrust dragging another sweet noise out of him. Tim looks so fucking gorgeous like this, with his mouth hanging open and his eyes glazed over with pleasure, his face bright red and his pretty dick straining against black lace. Jack reaches out to run his finger over Tim's bottom lip and Tim, the pretty little whore, wraps his lips around it. Tim moans when Jack shoves another in, his eyes fluttering shut as he licks and sucks at Jack's fingers. 

Stuffing Tim’s mouth does  _ nothing _ to quiet his pleasured whimpering, much to Jack's delight. "Fuck,  _ listen _ to you. My noisy little slut." Jack is rewarded with a precious whine and Tim opens his eyes, gazing up at Jack with a pleading expression that looks  _ much _ too sweet for someone desperately rocking against his cock. "Aw, what's the matter, sweetheart? You wanna cum?" Tim nods eagerly in response, and as much as Jack would _ love _ to hear him beg, he can’t deny that pretty face. "Yeah? Why don't you touch yourself then, huh?"

Tim reaches to rub his lace-covered cock, groaning around Jack's fingers and bucking up into his hand, desperate for the friction. He's leaking precum, and his dick jumps at the attention as he grinds his palm down against it.

_ "That's _ it," Jack urges through heavy panting, the sound of skin slapping against skin filling the room as he roughly fucks into Tim's perfect ass. "Come on, cum for me, baby."

Tim cries out, his back arching up off the bed as his whole body tenses up. He tosses his head back against the pillow and moans Jack's name, clawing down Jack's back as he cums in his panties.

Jack groans appreciatively at the way Tim clenches around him. When Tim finally relaxes against the bed, he's red faced and panting, and he looks almost dazed as he gazes up at Jack with half lidded eyes. "Cum inside me, Jack? Please?" he begs, sounding breathless. 

And  _ fuck,  _ how can Jack resist? He grips Tim's hips hard enough to bruise and slams into him, making Tim gasp with every thrust. "Can't wait to fill up this tight ass of yours, pumpkin. Gonna look fucking  _ perfect _ with my cum leaking out of you." Tim moans and yanks him down for another kiss, and Tim's enthusiasm is enough to push Jack over the edge. He groans into Tim's mouth as his thrusting loses its rhythm, and he bites down on Tim's lip as he cums inside him with a low grunt.

Panting, Jack presses his forehead against Tim's as he tries to catch his breath. Tim reaches up to run his fingers through Jack's hair, and the soft, sated smile on his face is  _ ridiculously  _ endearing. Jesus, Tim is so cute it ought to be illegal, and Jack can’t resist leaning down to give him a quick kiss. Then he pushes himself upright and shoves Tim's leg apart as he watches himself pull out. The lace of Tim's panties slides back into place, but Jack is quick to pull them out of the way.

Tim flushes when he realizes Jack is staring, but how can he  _ not?  _ Cum leaks out of Tim's perfect hole, and Jack admires his work, satisfied with the knowledge that he's staked a claim on Tim by popping his cherry. He reaches out to run his fingers through the sticky mess, making Tim squirm and close his legs with an embarrassed whine.

"Nuh-uh. Open 'em back up, princess." Jack is far too pleased with himself to give up that gorgeous view this soon. 

Actually…that thought gives him an idea.

Jack leans over Tim to grab his Echo from the nightstand, then pulls up the camera function. He aims the camera at that sweet ass, but he’s sure to get Tim’s pretty face in the shot, too.  _ "Now, _ pumpkin. Daddy wants a keepsake."

Tim groans in annoyance and rolls his eyes. "You're such a pervert," he complains, but he lets his legs fall open anyway, and pulls them up against his chest, leaving himself exposed. He reaches down to pull the panties out of the way again, presenting himself while Jack snaps the picture.

Jack lowers his Echo and smirks at Tim. Despite his protesting, he sure doesn't seem to mind posing for a dirty picture all that much. "Looks like I'm not the only one, huh sweetheart?" he says, before crawling over Tim to reward him with another kiss.

**Author's Note:**

> couldn't resist making jack a little soft on tim here because I'm also soft on tim


End file.
